I wonder if his apparent "careless" handling was rather intentional

[intrepidity]

You know, in his mafia-don way of doing things.

(tfg speaking to an "interested party" posing as a "guest" at MAL: "Someone might find something interesting if they went down such-and-such hall, opened such-and-such door (oh, and the key *might* be in such-and-such drawer) or looked in such-and-such closet. Hypothetically, of course." wink-wink)

[Claustrum]

1. I think one thing he is "smarter" than Nixon is that,

he learned that he can't just be "careless" in one instance. He abandoned all norms on all levels and everything he did so you can't pinpoint the instance of the "missing time" like Nixon. I think these documents are the same. There are some documents that are not secret or important (like Kim's love letter) while mixing in the real secret documents that he sold. And they all lay around on the floor all "carelessly" so you can't say there is just one outlier document.

[intrepidity]

2. Yep. He probably learned that way back when

he was a bouncing baby on Roy Cohn's knee.

[TheRealNorth]

3. That is my suspicion

Probably why they wanted the video tapes.